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Phosphoric Acid → HCID 70582695, Verbindung

HRID 261711
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 261711
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:21](=[O:22])[N:11]2[C:12]([C:18]([O-:20])=[O:19])=[C:13]([CH2:16][OH:17])[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na+].[C:24]([N:29]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[S:30]1(=[O:32])=[O:31])([O:26][CH2:27][CH3:28])=[O:25].C(N(CC)CC)C.P(=O)(O)(O)O>CN(C)C=O.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:21](=[O:22])[N:11]2[C:12]([C:18]([OH:20])=[O:19])=[C:13]([CH2:16][O:17][C:39](=[O:40])[C:38]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[S:30](=[O:32])(=[O:31])[NH:29][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 1004Phosphoric AcidHCID 8471Triethylamine2×HCID 227704Ethyl 3-oxo-1,2-benzothiazole-2(3h)-carboxylate 1,1-dioxideHCID 70582610Sodium 7beta-(t-butoxycarbonyl)amino-3-hydroxymethyl-3-cephem-4-carboxylate

Produkt 1

HCID 70582695HCID 70582695, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In dimethylformamide (20 ml) is dissolved sodium 7β-(t-butoxycarbonyl)amino-3-hydroxymethyl-3-cephem-4-carboxylate (3.20 g), followed by the addition of N-carboethoxysaccharin (3.20 g) and triethylamine (2.0 ml). The solution is stirred for one hour at room temperature and, after the addition of triethylamine (2.0 ml), stirred further for one hour. The solution is poured into toluene (1 L) and the resultant precipitate is collected by filtration, washed with toluene and dried. The powder thus obtained is dissolved in water (30 ml). After the addition of ethyl acetate (200 ml), the solution is adjusted to pH 4.0 with diluted phosphoric acid. After separation, the ethyl acetate solution is washed with water, dried over anhydrous sodium sulfate and concentrated. To the concentrate (30 ml), ether (200 ml) is added under stirring and the resultant precipitate is filtered off. The filtrate is concentrated under reduced pressure and to the concentrate (30 ml) is added carbon tetrachloride (100 ml). The resultant precipitate is collected by filtration, washed with carbon tetrachloride and dried over phosphorus pentoxide. The procedure provides 7β-(t-butoxycarbonyl)amino-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (2.50 g).

Aufarbeitung

  1. stirringstirred further for one hour
  2. filtrationthe resultant precipitate is collected by filtration
  3. washwashed with toluene
  4. customdried
  5. customThe powder thus obtained
  6. customAfter separation
  7. washthe ethyl acetate solution is washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. concentrationTo the concentrate (30 ml), ether (200 ml)
  11. additionis added
  12. stirringunder stirring
  13. filtrationthe resultant precipitate is filtered off
  14. concentrationThe filtrate is concentrated under reduced pressure
  15. concentrationto the concentrate (30 ml)
  16. additionis added carbon tetrachloride (100 ml)
  17. filtrationThe resultant precipitate is collected by filtration
  18. washwashed with carbon tetrachloride
  19. dry with materialdried over phosphorus pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-81ea8bef42224603a4b8b5c508e468d7
Quelldatensatz
uspto-grants-1979_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04166178

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